26.Gary Clark

Gary Clark lost his wife at Seattle Grace-Mercy West, and then he returned to the hospital with the intention of killing all of her doctors: Dr. Richard Webber (James Pickens Jr.), Dr. Derek Shepherd (Patrick Dempsey), and Dr. Lexie Grey (Chyler Leigh). While he roamed the halls with a loaded gun, he took many more lives than the three he was after. And then he found himself in a room with Richard and one bullet left. Richard told him he could shoot him and spend his life in jail or take his own life. And then, we just heard a gunshot. It wasn't until minutes later, when we saw Richard walking up to the police chief, that we realized what happened in that room. And you could only feel relief that Richard was OK and that Gary couldn't hurt anyone else. —Emily Orley

25.William Dunn

William Dunn was a serial killer on death row who was admitted to Seattle Grace Hospital with a spinal injury — one week before his scheduled execution. Cristina (Sandra Oh) gave him minimal care, and Derek associated him with his murdered father and had no sympathy for the killer, but Meredith (Ellen Pompeo) was more compassionate for once and provided Dunn with additional pain-management meds, listening to his rationalizations and empathizing with his mission to die on his own terms. She even helped him along by telling him exactly how he might cause his brain surgery to fail during post-op so that he could donate his organs to a child in organ failure who matched his blood type. But despite Dunn’s best efforts to sabotage his recovery, he was executed in prison as planned, with Meredith in attendance at Dunn’s request. Leave it to Meredith to form an empathic bond with the serial killer. —Andrea Battleground

24.Rachel Dawson

Rachel, her husband, Paul (Michael Buie), and her son Ethan (Kyle Red Silverstein) were in a car crash. Paul slipped into a coma, Rachel had immediate brain surgery, and it looked like poor Ethan was going to be an orphan. But Rachel got a bit better and Ethan went down to the cafeteria with her for some food. And then, she started seizing right in front of him. She was rushed to the elevator to get up to the operating room, but before the elevator could even make it to the right floor, she died. Of course you felt badly for this 10-year-old, but in 11 seasons' worth of episodes, Rachel was basically a stranger. —E.O.

23.Jimmy Evans

For a while there, Jimmy Evans was more of a myth in the Grey’s Anatomy world than a character: The drug-addict father's abuse and abandonment shaped Alex Karev (Justin Chambers). But that changed in Season 10 when Jimmy turned up as a flesh-and-blood heart patient at Grey Sloan Memorial. After several confrontations in which Jimmy slammed Alex’s girlfriend Jo (Camilla Luddington) into a wall and called his mom “bug-eyed crazy," the father and son looked to be on the road to a better relationship. Alex was coming to terms with his horror show of a childhood and seemed on the precipice of forgiveness, but then Shane (Gaius Charles) had a full-on meltdown, attempted Jimmy’s heart surgery solo, and instead ended up destroying the heart and killing the guy. If you ever felt for Alex, this was the time. —A.B.

22.Tommy Peterson

Morgan Peterson (Amanda Fuller) was an intern whom Alex took a liking to. She got pregnant, but then had a heart attack and was forced to deliver her baby at 24 weeks. Morgan, Alex, and Arizona (Jessica Capshaw) worked for weeks to keep the baby alive. But he was too small and had too many complications, so they decided it was time to remove all the tubes and let him die in his mom's arms, while Alex sat by her side. While Tommy wasn't much of a character, there are few things sadder than watching a baby die. —E.O.

21.Nick Hanscom

Nick Hanscom spent the first of his two episodes being charming and easygoing, and flirting with Lexie — so it was relatively easy to forget that he actually had a very exposed, very fragile carotid artery that needed repairing. But this is Grey’s Anatomy, after all, so of course that artery was going to burst…and it was going to burst all over Lexie right when he’d worked up the nerve to ask her out on a date. The poor guy bled out despite her best efforts. —A.B.

20.Charlie Yost (aka Really Old Guy)

Really Old Guy was basically in a comatose state for years. And then one day, he woke up — his vitals were good and Izzie (Katherine Heigl) was so excited to help him get back to his old life. But he didn't want that. All dressed and ready to be discharged, he slipped away in his wheelchair. It was bittersweet, because as disheartening as it was, it was also comforting to know he went on his own terms. —E.O.

19.Reed Adamson

Reed was a surgical resident at Seattle Grace Mercy West who was part of the new influx of residents who showed up following the hospital merger with Mercy West. She was roommates and friends with April Kepner (Sarah Drew), even coming to her defense when she was fired in one of their early episodes. But she was also the first victim of Gary Clark during the hospital shooting; he shot her in the head point-blank after she wouldn’t tell him where to find Derek. Reed's sudden death at the top of the episode was shocking and showed that the shooting would yield quite the body count and would leave all the characters reeling. Making it all the more horrifying, April was the one who discovered Reed’s body after she slipped in a pool of her friend’s blood. —A.B.

18.Mary Portman

Gary Clark entered Mary's room with a gun and shot Charles Percy (Robert Baker). She was spared, but a few months after the shooting, she returned to the hospital to have the textbook procedure she was scheduled to have that fateful day. And though the surgery went perfectly, Mary never woke up afterward. There was no indication why, and so her husband had to unplug her. And the irony was lost on no one. —E.O.

17.Francesca McNeil

Francesca “Frankie” McNeil and her two siblings were all pediatric patients with cardiomyopathy at Grey Sloan Memorial. Her sister, Ivy (Jadin Gould), was the first to receive a heart transplant, but her body rejected the new organ. Then, after receiving a pacemaker and an LVAD, Frankie was placed on the transplant list as well. With both sisters in heart failure, Cristina and the McNeils had to decide which of the two girls would receive the one heart available. Ivy was chosen because her chances of survival were greater, and despite Cristina’s best efforts to keep Frankie alive with an artificial heart, the girl died on the operating table, leaving the surgeon and parents to live with that impossible decision. —A.B.

16.Craig Thomas

Craig was Cristina's only friend in Minnesota. And he was a good one — he picked her up when her car was buried in snow! But when he was being forced to retire, he fought to do one more risky surgery. With Cristina's help, he won the surgery. AND THEN HE DROPPED DEAD IN THE MIDDLE OF IT. Literally, his eyes glazed over and he fell backward onto the ground. It was traumatic. This lovely man was in the midst of fulfilling his last wish and he just died before he could complete it. The only way to look at this glass half-full is that his death pushed Cristina to move back to Seattle. —E.O.

15.Heather Brooks

Heather was a member of the resident class who joined Grey Sloan Memorial in Season 9. She quickly rose from babysitting injured attending surgeons post–plane crash to discovering she had a real gift with neurosurgery, eventually beating out Shane to become Derek’s clear favorite resident and mentee. Just when Heather was starting to recognize her talent, get a handle on her insecurities, and accept her fate as a future neurosurgeon superstar, Season 10's superstorm struck. Alas, the ultra-competitive and downright devious Ross sent her on a fake errand that resulted in her electrocution, brain injury, and death — and it also set the stage for Ross' subsequent meltdown. —A.B.

14.Harold O'Malley

Mr. O'Malley was everyone's dad. I mean, he was really just George (T.R. Knight), Jerry (Greg Pitts), and Ronny's (Tim Griffin) dad. But he was so nice and caring that he made everyone feel like family. His tragic decline happened quickly. He passed out, hurt his shoulder, and ended up in the hospital. But while running routine tests, they found out he had cancer — and it was aggressive. George wanted to take the safest approach, but Harold told his doctors in a private moment he wanted the tumor cut out at all costs. After the surgery, he needed to be put on a ventilator. And when the tube needed to be replaced, they weren't able to fit a new one down his throat, leading to his death. Seeing George run outside and Cristina chase after him so she could tell him about being a member of the Dead Dads Club was just terrible to watch. —E.O.

13.Jen Harmon

Season 5 featured one crisis of fate after another and one of them surrounded Jen Harmon, a pregnant woman admitted to the hospital after an aneurysm forced her to run over her husband’s foot with their car. But the surgery to repair it kept getting delayed because of Derek’s more pressing neuro cases. When the delayed procedure finally happened, something went wrong and Jen had some complications. Derek operated on her brain again and that’s when things went disastrously, with him deciding to remove the woman’s temporal lobe. Eventually, the chief had to step in to let the poor woman die and the other surgeons save her baby. The failure to save Jen sent Derek into a downward spiral that had him quitting the hospital and hitting engagement rings with baseball bats. In an episode that featured an epic monologue from none other than Faye Dunaway, Jen's death was still pretty damn depressing. —A.B.

12.Adele Webber

Adele did not have an easy life. She stayed married to a man she knew was in love with someone else and then she was diagnosed with Alzheimer's. Her deterioration happened quickly and was closely watched as she entered Meredith and Derek's Alzheimer's trial. She became fearful of the world around her and was unable to recognize those trying to help her. In one of her final scenes, she found herself in the OR gallery hysterical. Richard was operating and started singing "My Funny Valentine," which made her believe it was their wedding night. She was crying, he was crying, and we were all crying. And then she died offscreen. Richard decided to still go to Bailey's (Chandra Wilson) wedding to tell Meredith (Ellen Pompeo) about Adele. Then they hugged because they're the only family either of them has left. Cue more crying. —E.O.

11.Ellis Grey

Ellis had many great qualities, but being a good mother was not one of them. Nor was being a compliant patient. She was difficult and hostile to her daughter and doctors all the time. But if Ellis was going to do one nice thing for her daughter, she picked a good time to do it. Ellis' heart started to fail as a "dead" Meredith decided she wanted to go back to be with Derek and Cristina and the rest of her friends. Ellis found Meredith in this purgatory-esque place, hugged her, and told her she's "anything but ordinary." Then, she had her daughter literally run for her life. It was a bait-and-switch: Ellis giving up on her life so her daughter could carry on with hers. And despite all the mean things she did and said to Meredith over the years, that act was not lost on anyone. Neither was the fact that Meredith couldn't let go of Ellis, because how do you say goodbye to your mother for the last time? You cannot without a whole lot of tears. —E.O.

10.Dylan Young

OH MY GOD THE HOMEMADE BOMB. When Meredith was pulling the bomb out of that (stupid) man's body, I was convinced it was going to explode. Bye, Mer. Bye, Burke (Isaiah Washington). Bye, everyone. But somehow it didn't. Dylan was a tough guy, and he was also a huge comfort to Meredith. He made sure that during the many hours she kept her hand on a bomb, she didn't move a single finger, let alone freak out. He even let Meredith imagine Derek's face in place of his! But just when you thought everyone was going to be fine, Dylan was blown up as he walked the bomb out of the building. He was so nice and risked his life because some dummy tried to make a bazooka bomb at home. It was shocking and heartbreaking. —E.O.

*Dylan returned in "Some Kind of Miracle" (Season 3, Episode 17) to help guide Meredith through the afterlife.

9.Charles Percy

OK, if I'm being honest, I was never invested in Percy as a character. He was one of the invaders from Mercy West and he was a tad annoying. BUT GOOD GRIEF HIS DEATH SCENE WAS PAINFUL. After being shot in a hospital room, Bailey determined he needed to get to the operating room. She and the patient in the room, Mary, dragged him to the elevator — and risked being seen by the shooter again — only to find it had been turned off for security purposes. At this point, there was nothing anyone could do but lie with him as he slowly bled out. He told Bailey he wanted to be brave and to find Reed and tell her he loved her (little did any of them know Reed had also been shot to death). And then, he took his last breath. GUH. —E.O.

8.Susan Grey

Part of me is still kind of convinced that Susan took some herbs or something to give herself hiccups to get her Thatcher (Jeff Perry) and Meredith to spend more time together. Just a small part! But then everything that could go wrong, did go wrong. I mean, who dies from the hiccups?! 1% of people, that's who. On top of watching her slowly decline over a period of days, you could visibly tell how truly terrified she was as her condition worsened. And with a dead mom and an asshole dad, Susan was really the only family Meredith had. Seeing her lose a pulse was so scary because it all happened so quickly. And then you just couldn't pick your jaw off the floor after Meredith told Thatcher Susan was gone and he SLAPPED HER. — E.O.

7.Mark Sloan

Mark Sloan had a reputation that preceded his arrival at Seattle Grace as Derek’s lothario of a best friend who up and seduced his wife. And just when Derek and Addison (Kate Walsh) decided to work it out, the man (the legend) himself arrived to wreak havoc on the fragile Seattle Grace community. Initially dubbed McSteamy, Sloan eventually grew into his own as a character and not simply a prop who disrupted relationships with his hotness. After becoming sex buddies with Callie (Sara Ramirez), he fostered an even deeper relationship with her, earning himself a new best friend and becoming the father of Callie’s child. Though he rallied once the survivors were discovered after Season 8’s plane crash, Mark's injuries were too great. After spending a few last moments with his daughter, he slipped into a coma, where he remained for a month before Callie made the decision to remove his life support. — A.B.

6.Henry Burton

Some may not recognize the true heartbreak that came from Henry's death, but I do. Henry was a kind, charming, considerate man. He cared so deeply for Teddy (Kim Raver), but he also really valued his relationship with each doctor at the hospital. So losing that lovely person was sad enough. But to watch as Cristina operated, unaware he was her patient, and wince at every move she made, was nerve-wracking. Each time his stats dropped, you were just quivering. And when she called time of death and ripped off her scrubs, you were sobbing. But wait, it got worse, because then you had to watch her learn that Henry was the man on her table. The whole thing was terrible, just terrible. —E.O.

5.Lexie Grey

When Lexie showed up as Meredith’s long lost half-sister in Season 3, there were a lot of barriers preventing her and Meredith from forging a sisterly bond. But they eventually did, despite the fact Lexie found out Meredith was one of the doctors who worked on her mom, Susan, prior to her death. After developing a crush on George that went absolutely nowhere, secretly performing surgeries with other interns, and having random hookups with Alex, Lexie fell in love with Mark. Which made it all the more tragic when he also died as a result of the plane crash, but at least they wouldn't have to figure out how to live without each other after finally realizing they were soulmates. —A.B.

4.Denny Duquette Jr.

Denny died alone. He died alone while Izzie kept changing her dress at home (though it's doubtful she could've done anything to stop a stroke). Denny didn't ask to have his LVAD wire cut, he just trusted Izzie. And then he somehow survived hours with nothing pumping to his heart. He also made it through a heart transplant in a very weak condition. After all that, after everything he had endured and overcome, fans thought, Phew, Denny is in the clear. But just when you took your eye off him, he formed a blood clot. It only took minutes for it to claim his life. It was fucking devastating. —E.O.

*Denny returned in "Some Kind of Miracle" (Season 3, Episode 17) to help guide Meredith through the afterlife. He also returned in Season 5 to warn Izzie that she was sick. "I'm here for you," he repeated over and over. Still crying.

3.Derek Shepherd

Truly, I never thought this day would come. I was convinced Grey's Anatomy would end with Meredith, Derek, Zola, and Bailey getting their happily ever after. And that is one of the many reasons this death was so damn painful. The second is Meredith. This woman has been through more in her life than anyone I know, real or fictional. And after surviving literally every disaster you could think of, she has to unplug her husband. ARE YOU SERIOUS?! And what a horrible way to go! I almost wish he had just died on impact from the truck if he HAD TO DIE. But having him survive only to die because some doctors didn't know what they were doing is that much more upsetting and terrifying. Also, with Cristina moving away in Season 10, it was just Derek, Meredith, Alex, Richard, and Bailey who remained from the beginning. They reminded truly loyal fans why they fell in love with this show 11 seasons ago. And now, we're another Grey's OG down. —E.O.

2.Doc

Doc was the canine friend Meredith adopted to get over Derek going back to his wife, Addison. But this was back when she, George, and Izzie still shared the big house, and the other two roommates didn’t warm to Doc’s shenanigans. (Remember when George said, “Cujo has to go!” and Meredith chose to keep the dog and let him move out? Oh, Meredith.) Eventually, Doc ended up living with Derek and Addison, with Meredith retaining visiting privileges. (I know, but let’s go with it.) It was soon revealed that Doc was ill, and Meredith started what is clearly a rebound relationship with the veterinarian, Finn (Chris O’Donnell). They discovered Doc had bone cancer, and rather than allow him to continue to suffer, Meredith elected to put the dog to sleep in one of the most heart-wrenching death scenes on the entire run of the show. —A.B.

1.George O'Malley

There was a collective scream heard round the world from Grey's Anatomy fans when those elevator doors opened and George was waiting for Izzie. Despite writing "007" on Meredith's hand and despite Callie recognizing a birthmark on John Doe, no one truly believed that George had been dragged by a bus to the point where he was not identifiable. He died from the injuries he sustained and it was the most shocking and upsetting moment in Grey's history. We are still not over it six seasons later. —E.O.

Honorable mentions:

We loved you. You were gone too soon (aka you were only alive in one episode):